python
diff --git a/docs/spec/directives.rst b/docs/spec/directives.rst
@@ -154,23 +154,157 @@ left undefined by the typing spec at this time.
 Version and platform checking
 -----------------------------
 
-Type checkers are expected to understand simple version and platform
-checks, e.g.::
+Type checkers should understand code paths as definitely reachable or not reachable due to comparison tests against these symbols:
+    * ``sys.version_info``
+    * ``sys.platform``
+    * ``sys.implementation.version``
+    * ``sys.implementation.name``
 
-  import sys
+Type checkers should support combining these checks with:
+    * A ``not`` unary operator
+    * An ``and`` or ``or`` binary operator
 
-  if sys.version_info >= (3, 12):
-      # Python 3.12+
-  else:
-      # Python 3.11 and lower
+Type checkers are only required to support the fully-qualified form (e.g., ``sys.platform``).
+Support for aliases or import variants (e.g., ``from sys import platform``) is not required, though type checkers may choose to support them.
 
-  if sys.platform == 'win32':
-      # Windows specific definitions
-  else:
-      # Posix specific definitions
+The comparison patterns for these variables are described in more detail in the following paragraphs.
 
-Don't expect a checker to understand obfuscations like
-``"".join(reversed(sys.platform)) == "xunil"``.
+sys.version_info checks
+^^^^^^^^^^^^^^^^^^^^^^^^
+
+Type checkers should support the following comparison patterns:
+    * ``sys.version_info >= <2-tuple>``
+    * ``sys.version_info < <2-tuple>``
+
+Comparison checks are only supported against the first two elements of the version tuple.
+It should be noted that type checkers may choose to also support the 3-tuple ``sys.version_info >= <3-tuple>``.
+Type checkers are not expected to support comparisons with named attributes of `sys.version_info`.
+
+.. code-block:: python
+   :caption: Example `sys.version_info`
+   :emphasize-lines: 2
+
+   import sys
+   if sys.version_info >= (3, 12):
+       # Python 3.12+
+   elif sys.version_info >= (3, 11):
+       # Python 3.11 
+   else:
+       # Python 3.10 and lower
+
+sys.platform checks
+^^^^^^^^^^^^^^^^^^^
+
+Type checkers should support the following comparison patterns:
+    * ``sys.platform == <string literal>``
+    * ``sys.platform != <string literal>``
+    * ``sys.platform.startswith(<string literal>)``
+    * ``sys.platform in <set of string literals>``
+    * ``sys.platform not in <set of string literals>``
+
+    Common values: ``"linux"``, ``"darwin"``, ``"win32"``, ``"emscripten"``, ``"wasi"``
+
+The membership checks ``in`` and ``not in`` only support simple containment testing with a set of literal strings.
+
+.. code-block:: python
+   :caption: Example `sys.platform`
+   :emphasize-lines: 2,4
+
+   import sys
+   if sys.platform == 'win32':
+       # Windows specific definitions
+   if sys.platform in ("linux", "darwin"):
+       # Platform-specific stubs for Linux and macOS
+       ...
+
+
+sys.implementation.name checks
+^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+Type checkers should support comparison patterns:
+    * ``sys.implementation.name == <string literal>``
+    * ``sys.implementation.name != <string literal>``
+    * ``sys.implementation.name in <set of string literals>``
+    * ``sys.implementation.name not in <set of string literals>``
+
+    Default value: ``"cpython"``, unless configured otherwise.
+    Common values: ``"cpython"``, ``"pypy"``, ``"micropython"``, ``"graalpy"``, ``"jython"``, ``"ironpython"``
+
+
+.. code-block:: python
+   :caption: Example `sys.implementation.name`
+   :emphasize-lines: 2,4
+
+   import sys
+   if sys.implementation.name == "cpython":
+       # CPython-specific stub
+   if sys.implementation.name == "micropython":
+       # MicroPython-specific stub
+
+
+sys.implementation.version checks
+^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+``sys.implementation.version`` is a tuple, in the same format as sys.version_info. However it represents the version of the Python implementation 
+rather than the version of the Python language. This has a distinct meaning from the specific version of the Python language to which the currently 
+running interpreter conforms. For CPython this is the same as `sys.version_info`.
+
+Type checkers should support the following comparison patterns:
+    * ``sys.implementation.version >= <2-tuple>``
+    * ``sys.implementation.version < <2-tuple>``
+
+Comparison checks are only supported against the first two elements of the implementation version tuple.
+Type checkers are not required to support comparisons against named attributes of `sys.implementation.version`.  
+
+.. code-block:: python
+   :caption: Example `sys.implementation.version`
+   :emphasize-lines: 2,4
+
+   import sys
+   if sys.implementation.name == "pypy" and sys.implementation.version >= (7, 3):
+       # PyPy version 7.3 and above
+   if sys.implementation.name == "micropython" and sys.implementation.version >= (1, 24):
+       # MicroPython version 1.24 and above
+
+
+No support for complex expressions
+^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+
+Type checkers are required to support the above patterns, and are not required to evaluate other comparisons or other syntax variants.
+
+Therefore checkers are **not required** to understand obfuscations such as:
+
+.. code-block:: python
+    :caption: Examples of unsupported or overly complex version/platform checks
+    :emphasize-lines: 4,6,8
+
+    import sys
+    from sys import platform
+
+    if "".join(reversed(sys.platform)) == "xunil": 
+        # Typecheckers will not be required to understand this obfuscated check
+    if platform == "linux":
+        # Typecheckers will not be required to understand this import alias for sys.platform
+    if "win" not in sys.platform:
+        # Typecheckers will not be required to understand this reversed membership check
+
+
+Configuration
+^^^^^^^^^^^^^
+
+Type checkers must provide configuration or CLI options to specify target ``sys.version``, ``sys.platform``, ``sys.implementation.name`` and ``sys.implementation.version``.
+
+================================  ==========================  ==============  ===========================================================================
+  Symbol                            Suggested Format            Example         Suggested Default
+================================  ==========================  ==============  ===========================================================================
+``sys.version``                   string ``"major.minor"``    ``"3.11"``      The version of the Python interpreter used to run the type checker.
+``sys.platform``                  lowercase string            ``"linux"``     The platform of the Python interpreter used to run the type checker.
+``sys.implementation.name``       lowercase string            ``"cpython"``   ``"cpython"`` unless configured otherwise.
+``sys.implementation.version``    string ``"major.minor"``    ``"3.14"``      The value used for ``sys.version`` unless configured otherwise.
+================================  ==========================  ==============  ===========================================================================
+
+The configuration options should allow users to specify the target values for these symbols, so that type checkers can evaluate the version and platform checks correctly.
+The exact mechanism and name for these configuration options is implementation-specific, and defined by each type checker.
 
 .. _`deprecated`: